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Local experiences
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Water Activities
Sailing

Best results for Sailing in Key West, FL

Showing 25-29 of 29 results

Sail Key West on a 2-Hour Champagne Sunset Cruise

Sail Key West on a 2-Hour Champagne Sunset Cruise

Sail into the Key West sunset with drinks and hors d'oeuvres included

Sail into the Key West sunset with drinks and hors d'oeuvres included

4.9 • 593 reviews

$123/ person

Sail a Private Historic Schooner in Key West

Sail a Private Historic Schooner in Key West

Private 2-hour sail on a 1939 wooden schooner in Key West

Private 2-hour sail on a 1939 wooden schooner in Key West

4.8 • 377 reviews

$1,345

Sail a Historic Schooner Sunset Cruise in Key West

Sail a Historic Schooner Sunset Cruise in Key West

Catch the Key West sunset on the historic schooner Malabar X

Catch the Key West sunset on the historic schooner Malabar X

4.8 • 377 reviews

$124/ person

Private Schooner Sunset Sail in Key West

Private Schooner Sunset Sail in Key West

Charter a 1939 wooden schooner for a sunset sail from Key West’s Historic Seaport

Charter a 1939 wooden schooner for a sunset sail from Key West’s Historic Seaport

4.8 • 377 reviews

$2,474

Private 3-Hour Sailing Lesson in Key West

Private 3-Hour Sailing Lesson in Key West

Choose your boat and learn to sail with a private instructor in Key West

Choose your boat and learn to sail with a private instructor in Key West

4.9 • 49 reviews

$143& up

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